Dale, A look at the Google hits on ‘pimp the system’ tells me that it seems to mean to ‘milk’ or ‘exploit’ the system for all it is worth. The ‘pimp’ comes in as a verb since it describes how a ‘pimp’ (usually a man) exploits his prostitutes. I don’t see where it necessarily means doing anything illegal, but it involves taking advantage of the system to the fullest. Of the nearly 5000 hits I got, most referred to a rap song of this name (see below). Note that the first quote below bears some relevance to our present site problems:
<2002 “While you can PIMP THE SYSTEM now by getting multiple logins, even I (a non-database type) could pull this off
fairly easily.”— QC Ratings: Round 2 – Robert Lee, 11 June>
<2003 “The ‘street politics’ that Cube refers to are addressed in songs such as "Pimp the System," which contains the line "Your prostitutes wear high-heeled boots/ My prostitutes wear three-piece suits." "It's all about taking that (pimping) mentality corporate," Cube told VH1, "figuring out how to make money the legal way, which is a new way of thinking.”—‘Albuquerque Journal,’ 26 December>
In Brooklynese (and a few other dialects) a ‘gangster’ is a ‘gangsta’ and your ‘mother’ is you ‘motha’ — I think you get the idea.
Ken G – December 22, 2004
Reply from Ken Greenwald (Fort Collins, CO - U.S.A.)